To whatever extent, no one likes being trapped in boring chitchats. That is why it’s always fun when conversations keep going with lots of interesting twists and nuances. It’s no secret that one of the best ways to keep a conversation alive and interactive is to ask an infinite amount of questions. Make the questions funny—or at least evocative of funny answers—and you’re all set for a delightful conversation!

While this list sets its demographic towards guys, it’s actually quite general and apt for mostly anyone. It’s just that the best kind of people to ask these questions to are guys. These questions get an increase in effectiveness that way.

So, whenever you’re in a situation where you need to break the ice or simply initiate a social conversation with a guy, feel free to use this list. Do note that this list of questions may or may not be funny per se, but the resulting answers have great potential to spark fun and keep the conversation flowing.

What’s the funniest joke that you can think of right now?

What is one food that you consider the bane of your existence?

If your life had a theme song, what would it be?

What is something that I wouldn't believe about you?

What is the most hilarious childhood experience that you could think of right now?

What do you think you would be doing if you never had to work in your life?

Have you ever noticed that easy open packages never seem to open that easily?

If you manage to survive the apocalypse, what do you think your post-apocalyptic job would be?

What’s the most imaginative insult you can come up with right now?

How do you handle people you don’t like?

Which came first, the egg or the chicken?

Where do you want to be in an hour?

What is the color of your underwear right now?

What song do you feel the absolute urge to sing along with whenever you hear it?

What’s the one thing that you’re most terrible at?

Do you consider yourself more of a nice person or a naughty person?

What commercial convinced you not to buy the product they are advertising?

What conspiracy theories do you believe in?

What do you think am I thinking right now?

What do you think is the worst way to die?

What makes you cry?

How many walkers have you killed? How many people? Why?

When it comes to toilet paper, do you set the flap over or under?

What three things you would never spend your money on?

If animals could talk, which do you think would be the rudest?

What is something that is really important to you but you never get the chance to talk about?

What small stuff do you always sweat?

For you, what does the perfect burger look like?

What can you talk about for hours on end?

What’s the most absurd thing that has become a reality for you?

What’s your biggest kitchen fail?

What do you consider the sexiest animal on the planet?

Given the chance, what would you say to your five year old self?

Are you happy right now?

What is the longest amount of time you have been awake?

What common piece of advice or words of wisdom don’t actually make much sense?

What's your favorite smell?

What is your signature dance move?

Are you concerned with what other people think about you?

What’s one super power that you would never want to have?

What’s your definition of a good human being?

What is something that everyone looks stupid doing?

What’s the craziest thing you’ve ever done?

If you were a pizza topping, what would you be and why?

What’s the most terrible movie that you love?

If you were a rapper, what would your rapper name be?

Would you rather always say everything that goes in your mind or never speak a word again?

Could you go for a month without any kind of electronic gadget?

Can you fold a fitted sheet?

What’s the weirdest smell you have ever smelled?

Would you rather have bionic arms or bionic legs?

Does your credit card have three numbers on the back like mine? What are they?

What’s the worst thing you have ever tasted?

What are some things that are okay to do occasionally but definitely not okay to do everyday?

Would you like to be famous? In what way?

What is the most normal thing about you?

If you had to flee the country, where would you choose to live?

What was the last thing in your mind?

If you were to tell me three things about yourself right now, which two things are total lies?

Would you rather have the ability to fly or teleport?

What would be the creepiest thing you could say while passing by a stranger on the street?

What is the most embarrassing thing you have ever worn?

If you could anywhere in the universe for one day, where would you go?

What inanimate object do you wish you could eliminate from existence?

If you could eat only one kind of food for the rest of your life, what would it be?

What is something that is really popular now, but in 10 years everyone will look back on and be embarrassed by?

What are you proud of but never have an excuse to talk about?

What is the most stupid way you’ve ever hurt yourself?

What is the funniest name you have actually heard used in the real world?

What takes most of your time in your everyday life?

What is the weirdest thing you have seen in someone’s house?

What are you too old to do but still enjoy doing?

What flavor combination is kind of weird but you really like it?

What mythical creature would improve the world the most if it existed?

Would you cannibalize someone to survive on a stranded island knowing that there's a 25% chance of rescue/survival if you eat the corpse but a guaranteed death if you don't eat it?

What movie would improve drastically if it was turned into a musical?

What’s the first thing that you do when you get home?

If you could pick a day to relive over and over in a never-ending loop, what day would it be and why?

If you had to replace your hands with something else, what would you put at the end of your arms?

If you could make one absolute rule for a day that everyone should follow, what would it be?

If you had to become an inanimate object for a month, what object would you choose to be and why?

What was your dream job when you were a child?

What’s one thing that you refuse to share no matter what?

Where is the strangest place you’ve ever peed or pooped?

Which is better to listen to, your heart or your brain?

On a scale of 1-10, how old are you?

If you had a disease named after you, what would be the symptoms?

If you were to die tomorrow, why not now?

What is the funniest joke you know by heart?

What is something that you used to know was true, but no longer is?

Would you rather have noisy neighbors or nosy neighbors?

What’s your weirdest pet-peeve?

What color is your toothbrush?

Why do guys have nipples?

Who is your favorite villain?

What’s the dumbest rule you’ve been forced to follow?

What rules do you make for yourself?

If you were given the chance to marry any fictional character, who would it be?

If you were imprisoned for something bad you did, what would your crime be?

How can we rob this place?

Which character from any show would you want to kill if you had the chance?

What secret conspiracy would you like to start?

Have you ever stolen anything?

Has anyone ever walked in on you naked?

If you had to be on an isolated island with only one book, which one would it be?

When was the last time you peed in a pool?

What’s your favorite animal sound?

What kind of cult would you like to start?

Do you like waking up early or staying up late?

Which actor would be best to play you in a movie about your life?

What would you choose as your animal sidekick if you were in a movie?

You are about to get into a fight, what song comes on as your soundtrack?

What is the weirdest nickname people have ever called you?

Would you rather fight a horse-sized duck or a hundred duck-sized horses?

Of all your pet-peeves, which one is the strangest?

Would you rather be able to only whisper or only shout everything?

Which fictional character do you identify with the most?

What superpower do you want to have?

What song would you play on repeat if you had to torture someone with it?

How would you get yourself fired if you could?

In one sentence, how would you sum up your life?

Would you rather eat raw egg for the rest of your life or sleep in a bathtub filled with egg yolk for a year?

What is the cheesiest pickup line you’ve ever tried?

What would be the worst “buy one get one free” sale of all time?

What turns you on?

How often does your brain go on autopilot?

What would your last words be?

What is the most interesting piece of trivia you know?

If you were a ghost, how would you haunt people?

What do you know way too much about?

What random acts of extreme kindness would you like to see?

What was the last movie that made you cry?

What song do you want played while your coffin is being dropped six foot below?

What do you think is the most useless major in college?

What do you think you know a lot about but probably don’t?

What is your favorite thing to wear to bed?

What game do you dominate when you play it?

What job doesn’t exist but should?

What did you think was silly until you tried it?

What’s the worst lie you’ve ever told someone?

I think I have lost my phone number, can i have yours?

What’s the weirdest thing you used to eat as a child?

What was fun to do once, but you’ll never try to do again?

What is the most irritating food for you?

What one question can you ask someone to find out the most about them?

What would be the absolute best pet to have?

What is something that most people get wrong about you?

What happened the last time you almost died?

What’s the weirdest crush you’ve ever had?

What childish thing do you still enjoy?

What was the worst purchase you’ve ever made?

How many chickens would it take to kill an elephant?

What’s the first thing you would do if a zombie apocalypse breaks out?

When you are day dreaming, what do you dream about?

What is the most boring activity imaginable?

What was the random compliment that someone gave you that really got stuck in your memory?

What would you recommend to someone if they had the day off and didn’t know what to do?

What’s the most important file on your computer?

What’s the best WiFi name you’ve seen?

What scene from a movie scarred you for life?

What was the weirdest habit you had as a child?

What’s something everyone should experience at least once in their life?

What are some of the nicknames you have for your friends?

What is something most people do easily but you find very difficult to do?

If you could level up in life just like in video games, where would you put your next skill point?

If time wasn’t an issue and you had forever to master a skill, what skill would you like to master?

What’s the best prank you’ve ever played on someone?

What would be the worst thing to have a phobia of?

What do you think is the most common complaint people in your country have?

What would be the most spectacular funeral you could imagine?

What small thing makes you angrier than it should?

What do you own that a lot of people comment on?

What movie can you watch over and over and never get tired of?

What’s the most paranormal thing that has ever happened to you?

What do you judge people for that you probably shouldn’t?

What double standard is ridiculous and needs to be ended?

What part of your body would you replace with an improved mechanical version?

What is the strangest thing that ever happened to you?

What would the world be like if it was filled with male and female copies of you?

Which animal would be the worst to be eaten by?

If you had to be stuck at one age forever, what age would you choose and why?

What looks like it should taste better than it does?

What was the most historic thing that you witnessed in person or took part in?

When was the last time you remembered someone doing or saying something so stupid that you were sure it was a joke?

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